Water → 6-(azidomethyl)-N-[(4-chlorophenyl)methyl]-1-methyl-4-oxo-quinoline-3-carboxamide

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A solution of N-(4-chlorobenzyl)-6-(chloromethyl)-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide from Preparation No. 35 (200 mg) and sodium azide (176.8 mg) in anhydrous DMF (7 mL) is heated at 60° C. overnight. The reaction is cooled to room temperature and poured into water to precipitate the product. The solid is adsorbed onto silica and purified by chromatography (eluent 100% CH2Cl2 (1 L), 0.5% MeOH in CH2Cl2 (1 L), and 1% MeOH in CH2Cl2 (1 L)). Fractions homogenous by TLC were combined and concentrated to afford 182.7 mg (90%) of the title compound as a white solid.

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